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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:50:52 UTC

Update Date

2023-02-21 17:22:32 UTC

HMDB ID

HMDB0032629

Secondary Accession Numbers

HMDB32629

Metabolite Identification

Common Name

2',5'-Dihydroxyacetophenone

Description

2',5'-Dihydroxyacetophenone, also known as 2-acetylhydroquinone or 1-(2,5-dihydroxyphenyl)-ethanone, belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. Based on a literature review very few articles have been published on 2',5'-Dihydroxyacetophenone.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-(2,5-Dihydroxyphenyl)-ethanone	HMDB
1-(2,5-Dihydroxyphenyl)ethanone, 9ci	HMDB
1-Acetyl-2,5-dihydroxybenzene	HMDB
2', 5'-Dihydroxyacetophenone	HMDB
2',5'-Dihydroxy-acetophenone	HMDB
2,5-Dihydroxy-1-acetylbenzene	HMDB
2,5-Dihydroxyacetophenone	HMDB
2,5-Dihydroxyphenyl methyl ketone	HMDB
2-Acetyl-1,4-dihydroxybenzene	HMDB
2-Acetylhydroquinone	HMDB
Acetylhydroquinone	HMDB
Acetylquinol	HMDB
Ghl.PD_Mitscher_leg0.355	HMDB
Quinacetophenone	HMDB

Chemical Formula

C₈H₈O₃

Average Molecular Weight

152.1473

Monoisotopic Molecular Weight

152.047344122

IUPAC Name

1-(2,5-dihydroxyphenyl)ethan-1-one

Traditional Name

1-(2,5-dihydroxyphenyl)ethanone

CAS Registry Number

490-78-8

SMILES

CC(=O)C1=C(O)C=CC(O)=C1

InChI Identifier

InChI=1S/C8H8O3/c1-5(9)7-4-6(10)2-3-8(7)11/h2-4,10-11H,1H3

InChI Key

WLDWSGZHNBANIO-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Acetophenone
Aryl alkyl ketone
Hydroquinone
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032629)
Cytoplasm (HMDB: HMDB0032629)

Source

Endogenous

Endogenous (HMDB: HMDB0032629)

Exogenous

Food

Food (HMDB: HMDB0032629)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	202 - 203 °C	Not Available
Boiling Point	329.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	15070 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.274 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	9.21 g/L	ALOGPS
logP	1.21	ALOGPS
logP	1.57	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	9.42	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	40.42 m³·mol⁻¹	ChemAxon
Polarizability	14.84 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.552	31661259
DarkChem	[M-H]-	129.656	31661259
DeepCCS	[M+H]+	133.49	30932474
DeepCCS	[M-H]-	129.772	30932474
DeepCCS	[M-2H]-	167.506	30932474
DeepCCS	[M+Na]+	143.045	30932474
AllCCS	[M+H]+	131.2	32859911
AllCCS	[M+H-H2O]+	126.6	32859911
AllCCS	[M+NH4]+	135.5	32859911
AllCCS	[M+Na]+	136.7	32859911
AllCCS	[M-H]-	127.5	32859911
AllCCS	[M+Na-2H]-	128.8	32859911
AllCCS	[M+HCOO]-	130.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2',5'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=CC(O)=C1	2082.8	Standard polar	33892256
2',5'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=CC(O)=C1	1402.9	Standard non polar	33892256
2',5'-Dihydroxyacetophenone	CC(=O)C1=C(O)C=CC(O)=C1	1589.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2',5'-Dihydroxyacetophenone,1TMS,isomer #1	CC(=O)C1=CC(O)=CC=C1O[Si](C)(C)C	1624.9	Semi standard non polar	33892256
2',5'-Dihydroxyacetophenone,1TMS,isomer #2	CC(=O)C1=CC(O[Si](C)(C)C)=CC=C1O	1569.2	Semi standard non polar	33892256
2',5'-Dihydroxyacetophenone,2TMS,isomer #1	CC(=O)C1=CC(O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	1656.0	Semi standard non polar	33892256
2',5'-Dihydroxyacetophenone,1TBDMS,isomer #1	CC(=O)C1=CC(O)=CC=C1O[Si](C)(C)C(C)(C)C	1890.3	Semi standard non polar	33892256
2',5'-Dihydroxyacetophenone,1TBDMS,isomer #2	CC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O	1818.4	Semi standard non polar	33892256
2',5'-Dihydroxyacetophenone,2TBDMS,isomer #1	CC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2128.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2',5'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-1900000000-1be284ecaa5ed9b87e30	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',5'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-1900000000-8e9a7c4012d3cd5b5c54	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',5'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-5900000000-e57c3609fe3f8770c9bb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',5'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-1900000000-1be284ecaa5ed9b87e30	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',5'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-1900000000-8e9a7c4012d3cd5b5c54	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2',5'-Dihydroxyacetophenone EI-B (Non-derivatized)	splash10-0f79-5900000000-e57c3609fe3f8770c9bb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',5'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0k9i-2900000000-235bba6b3601c104f113	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',5'-Dihydroxyacetophenone GC-MS (2 TMS) - 70eV, Positive	splash10-00e9-5590000000-931c8c54df585b310163	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2',5'-Dihydroxyacetophenone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udi-0900000000-9878170510ac3d77cff5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0udi-0900000000-3362d1093c07449625cc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-052u-9700000000-4bf4a2446f7285b8d6cc	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-6f9f415d948ef9315b1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0udi-0900000000-49d0fea70f9f972ce4f5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-0a4i-5900000000-7eae2dee8e3d813b3dc4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 10V, Negative-QTOF	splash10-0udi-0900000000-1750905022a298264c01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 20V, Negative-QTOF	splash10-0pb9-0900000000-cf2ffdadd5622b737272	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 40V, Negative-QTOF	splash10-014i-9200000000-7aef573e2ef5ce48d40f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 10V, Positive-QTOF	splash10-0udr-0900000000-702c2e3b8485cb73217a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 20V, Positive-QTOF	splash10-0k9l-2900000000-9413cf547a88dfc11e04	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2',5'-Dihydroxyacetophenone 40V, Positive-QTOF	splash10-0f6x-9100000000-145ce1c01cb17fe62681	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB010573

KNApSAcK ID

Not Available

Chemspider ID

9859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10279

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1157781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2',5'-Dihydroxyacetophenone (HMDB0032629)

MOL for HMDB0032629 (2',5'-Dihydroxyacetophenone)

3D MOL for HMDB0032629 (2',5'-Dihydroxyacetophenone)

3D SDF for HMDB0032629 (2',5'-Dihydroxyacetophenone)

3D-SDF for HMDB0032629 (2',5'-Dihydroxyacetophenone)

PDB for HMDB0032629 (2',5'-Dihydroxyacetophenone)

3D PDB for HMDB0032629 (2',5'-Dihydroxyacetophenone)

SMILES for HMDB0032629 (2',5'-Dihydroxyacetophenone)

INCHI for HMDB0032629 (2',5'-Dihydroxyacetophenone)

Structure for HMDB0032629 (2',5'-Dihydroxyacetophenone)

3D Structure for HMDB0032629 (2',5'-Dihydroxyacetophenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra